3-methyl-1,2-hexadiene | 7736-41-6

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 3-methyl-1,2-hexadiene
• 英文别名: 3-methyl-hexa-1,2-diene；3-Methylhexa-1,2-diene
• CAS: 7736-41-6
• 化学式: C₇H₁₂
• 分子量: 96.1723
• InChiKey: NLMUJSVKDJTCSV-UHFFFAOYSA-N

物化性质

• 沸点：
  94.5-96 °C(Press: 680 Torr)
• 密度：
  0.7359 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-methyl-1,2-hexadiene 、 二苯基二硒醚 、 二苯二硫醚 以 氘代氯仿 为溶剂， 反应 5.0h， 生成 Z-3-methyl-2-(phenylseleno)-1-(phenylthio)-2-hexene 、 E-3-methyl-2-(phenylseleno)-1-(phenylthio)-2-hexene
  参考文献：
  名称：

  A Novel Photoinduced Thioselenation of Allenes by Use of a Disulfide−Diselenide Binary System

  摘要：

  Dependent on the selection of the lights employed, the relative.reactivities of organic dichalcogenides toward carbon radicals, and the thermodynamical stability of products, it has become apparent that two different chalcogeno groups can be introduced simultaneously into allenes with excellent selectivity. The (PhS)(2)-(PhSe)(2) binary system is effective for the regioselective thioselenation of allenes, affording beta-selenoallylic sulfides in good yields. Further investigation on the reaction of allenes with (PhS)(2) and (PhTe)(2) afforded no thiotelluration products, unfortunately, due to the instability of C-Te bonds under photoirradiated conditions. However, a novel telluride-catalyzed dithiolation reaction of allenes with disulfides has been developed successfully, while the use of a disulfide single system could not effect the radical dithiolation of allenes.

  DOI：

  10.1021/jo972253p
• 作为产物：
  描述：

  (Z)-2-chloro-3-methylhex-2-ene 、 氨基钠 以70%的产率得到
  参考文献：
  名称：

  VOSKANYAN, EH. S.;AKOPYAN, O. G.;MKRTCHYAN, A. M.;GASPARYAN, S. M.;SHAXBA+, ARM. XIM. ZH., 41,(1988) N 7, S. 411-415

  摘要：

  DOI：

文献信息

• Polylithiumorganic compounds
  作者：Adalbert Maercker、Andrea Tatai、Burkhard Grebe、Ulrich Girreser

  DOI：10.1016/s0022-328x(01)01195-0

  日期：2002.1

  observed. The metalation products 5–7 show follow-up reactions like 1,3-H shift to the corresponding 1-lithio-1-alkynes 8 and subsequent metalation to the dilithioalkynes 9. Additionally, lithium hydride elimination and ring-chain rearrangement (for 5c) are observed. 1,2-Hexadiene (3b) can be brought to reaction with lithium metal in the apolar solvent pentane, here the follow-up reactions are much slower

  研究了丙烯（3a）与烷基取代的丙烯1,2-己二烯（3b），环丙烯（3c）和亚乙烯基环丙烷（3d）与锂金属的反应，以获得2,3-二硫代烯烃4a - d。这些二硫代烯烃4a - d在极性溶剂（如THF）中具有很高的反应性，并作为强碱，可以观察到起始丙二烯3a - d或该溶剂的金属化或足够酸性的中间体（如8 a - d）。金属制品5 – 7显示后续反应，如1,3-H转移到相应的1-lithio-1-炔烃8和随后的金属化到dilithioalkynes 9。此外，观察到氢化锂消除和环链重排（对于5c）。1,2-己二烯（3b）可以在非极性溶剂戊烷中与锂金属反应，由于4b的不溶性，因此后续反应要慢得多。在所有情况下，通过用简单的亲电试剂淬灭，形成区域异构体和立体异构体产物的复杂混合物阻碍了对反应途径的阐明。
• A Novel Photoinduced Thioselenation of Allenes by Use of a Disulfide−Diselenide Binary System
  作者：Akiya Ogawa、Ryoichi Obayashi、Mikio Doi、Noboru Sonoda、Toshikazu Hirao

  DOI：10.1021/jo972253p

  日期：1998.6.1

  Dependent on the selection of the lights employed, the relative.reactivities of organic dichalcogenides toward carbon radicals, and the thermodynamical stability of products, it has become apparent that two different chalcogeno groups can be introduced simultaneously into allenes with excellent selectivity. The (PhS)(2)-(PhSe)(2) binary system is effective for the regioselective thioselenation of allenes, affording beta-selenoallylic sulfides in good yields. Further investigation on the reaction of allenes with (PhS)(2) and (PhTe)(2) afforded no thiotelluration products, unfortunately, due to the instability of C-Te bonds under photoirradiated conditions. However, a novel telluride-catalyzed dithiolation reaction of allenes with disulfides has been developed successfully, while the use of a disulfide single system could not effect the radical dithiolation of allenes.
• VOSKANYAN, EH. S.;AKOPYAN, O. G.;MKRTCHYAN, A. M.;GASPARYAN, S. M.;SHAXBA+, ARM. XIM. ZH., 41,(1988) N 7, S. 411-415
  作者：VOSKANYAN, EH. S.、AKOPYAN, O. G.、MKRTCHYAN, A. M.、GASPARYAN, S. M.、SHAXBA+

  DOI：——

  日期：——